The present invention relates to an information processing device, an information processing method, and a program that make it possible to prevent recommendation in a CF method from concentrating on a part of contents, and recommend a content to a user with little history information. In step S11, another user X having most similar history information to that of a user A to whom to recommend a musical piece is detected. In step S12, a musical piece a that the user X has and which the user A does not have is detected. In step S13, a cluster in each cluster layer to which the musical piece a belongs is identified. Then, in step S14, common musical pieces classified into all the clusters identified are extracted and set as recommendation candidates. Further, in step S15, one musical piece that has most similar cluster information to that of the musical piece a is selected among the musical pieces as recommendation candidates. The musical piece selected in this step is recommended to the user A. The present invention is applicable to content selling sites set up on the Internet, for example.